Synthesis of 1, 3, 4-thiadiazol-2(3H)-one derivatives via an unexpected intramolecular addition-elimination reaction of 1, 3, 4-thiadiazoles. Issue 30 (27th July 2017)

• Record Type: Journal Article
• Authors: Tahtaci, Hakan; Er, Mustafa; Karakurt, Tuncay; Sancak, Kemal
• Is Part Of: Tetrahedron. Volume 73:Issue 30(2017)
• Page Start: 4418
• Page End: 4425
• Publication Date: 2017-07-27
• Subjects: 1, 3, 4-Thiadiazole -- 1, 3, 4-Thiadiazol-2(3H)-one -- Intramolecular addition-elimination reaction -- A novel method; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.06.006
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A new synthesis was developed for 1, 3, 4-thiadiazol-2(3 H )-one derivatives, based on a new arrangement on the thiadiazole ring with an intramolecular addition-elimination reaction. To this end, starting from 5-methyl-1, 3, 4-thiadiazole-2-thiol(1), derivatives of 3-((un)substituted benzyl)-5-methyl-1, 3, 4-thiadiazol-2(3 H )-one(7a-g) and ((un)substituted phenyl)-2-oxoethyl)-5-methyl-1, 3, 4-thiadiazol-2(3 H )-one(10–15) were synthesized (in yields of 81–88% and 63–71%, respectively). The structures of all synthesized compounds were characterized using IR, 1 H NMR, and 13 C NMR spectroscopy, and elemental analysis, mass spectroscopy and X-ray diffraction analysis (compounds3c, 7b-f and10 ) techniques. This study presents a new and effective reaction path for the synthesis of 1, 3, 4-thiadiazol-2(3 H )-one derivatives. Graphical abstract: Highlights: This study exhibits a new and effective method to synthesize target compounds. A new method of synthesis was developed for 1, 3, 4-thiadiazol-2(3 H )-one derivatives. Not only this method takes less time to perform, but it also costs less. The synthesized compounds were characterized by different spectroscopic techniques.